Synthesis, characterization, morphology and adsorption performance towards cu+2 ions of nano-sized copolymers of anthranilic acid and o-aminophenol poly(anthranilic acid-co-o-aminophenol)


Nanospheres with different particles size and nanorodes of copolymer of anthranilic acid with o-aminophenol poly(AA-co-o-AP) were synthesized by redox polymerization initiated by FeSO4.7H2O as redox initiator and ammonium peroxydisulfate (APS) as oxidant in different concentrations of aqueous solutions of hydrochloric acid. The influence of synthetic parameters such as acid concentration and the presence of redox initiator were investigated. The morphology and particles size were studied by transmission electron microscope (TEM) and scanning electron microscope (SEM). The results showed that the morphology and average particle size of polymeric nano particles according to SEM and TEM analyses were different based upon the conditions of the copolymerization. The physico-chemical characterization of the prepared nanoparticles was carried out by Fourier transform infrared spectroscopy (FT-IR), X-ray powder diffraction (XRD) and Thermogravimetric(TGA). Which FT-IR confirmed the structure of poly(AA-co-o-AP) nanoparticles in emeraldine form. The molecular weight was determined by gel permeation chromatography (GPC). The surface area of nanocopolymer particles was determined also by Brunauer-Emmett-Teller (BET). The competition of the prepared nano-sized copolymers particles towards the adsorption of copper ions from aqueous solutions was investigated. The results showed that the adsorption capacity was based on particle size of nanocopolymers and their surface area. The adsorption capacity increased with decreasing the particle size. On the other hand the adsorption capacity increased with increasing the surface area and the molecular weight of the prepared nano-sized copolymers of poly(AA-co-o-AP).

This is a preview of subscription content, access via your institution.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5


  1. 1.

    Khalil AA, Shaaban AF, Azab MM, Mahmoud AA, Metwally AM (2013) Synthesis, characterization and morphology of polyanthranilic acid micro- and nanostructures. J. Polym. Res. 20:142–152

    Article  CAS  Google Scholar 

  2. 2.

    Mallakpour S, Behranvand V (2016) Polymeric nanoparticles: recent development in synthesis and application. Express Polym Lett 10:895–913

    Article  CAS  Google Scholar 

  3. 3.

    Mohanraj VJ, Chen Y (2006) Nanoparticles. Trop. J. Pharm. Res. 5:561–573

    Google Scholar 

  4. 4.

    Mahalingam M, Krishnamoorthy K (2015) Selection of a suitable method for the preparation of polymeric nanoparticles. Adv Pharm Bull 5:57–67

    PubMed  PubMed Central  CAS  Google Scholar 

  5. 5.

    Crucho CIC, Barros MT (2017) Polymeric nanoparticles: a study on the preparation variables and characterization methods. Mater. Sci. Eng. C 80:771–784

    Article  CAS  Google Scholar 

  6. 6.

    Hornig S, Heinze T, Becer CR, Schubert US (2009) Synthetic polymeric nanoparticles by nanoprecipitation. J. Mater. Chem. 19:3838–3840

    Article  CAS  Google Scholar 

  7. 7.

    Schmid G (2004) Nanoparticles: from theory to applications. Willey-VCH Publishers, Weinheim

    Google Scholar 

  8. 8.

    Geckeler KE, Rosenberg E (eds) (2006) Functional nanomaterials. American Scientific Puplishers, Valencia

    Google Scholar 

  9. 9.

    Hosokawa M, Nogi K, Yokoyama T (2007) Nanoparticle technology handbook. Elseiver, Amsterdam

    Google Scholar 

  10. 10.

    Geckeler KE, Nishide H (eds) (2010) Advanced nanomaterials. Willey-VCH Publishers, Weinheim

    Google Scholar 

  11. 11.

    Wang X, Summers CJ, Wang ZL (2004) Large-scale hexagonal-patterned growth of aligned ZnO nanorods for nano-optoelectronics and nanosensor arrays. Nano Lett. 4:423–426

    Article  CAS  Google Scholar 

  12. 12.

    Jang JS, Oh JH (2002) Novel crystalline supramolecular assemblies of amorphous polypyrrole nanoparticles through surfactant templating. Chem. Commun. 19:2200–2201

    Article  CAS  Google Scholar 

  13. 13.

    Fudouzi H, Xia Y (2003) Photonic papers and inks: color writing with colorless materials. Adv. Mater. 15:892–896

    Article  CAS  Google Scholar 

  14. 14.

    Brahim S, Narinesingh D, Elie GA (2001) Amperometric determination of cholesterol in serum using a biosensor of cholesterol oxidase contained within a polypyrrole-hydrogel membrane. Anal. Chim. Acta 448:27–36

    Article  CAS  Google Scholar 

  15. 15.

    Zhang Q, Chuang KT (2001) Adsorption of organic pollutants from effluents of a Kraft pulp mill on activated carbon and polymer resin. Adv. Environ. Res. 5:251–258

    Article  CAS  Google Scholar 

  16. 16.

    Nagavarma BVN, Yadav HKS, Ayaz A, Vasudha LS, Shivakumar HG (2012) Different techniques for preparation of polymeric nanoparticles. Asian J Pharm Clin Res 5:16–23

    CAS  Google Scholar 

  17. 17.

    Staff RH, Landfester K, Crespy D (2013) Recent advances in the emulsion solvent evaporation technique for the preparation of nanoparticles and nanocapsules. Adv. Polym. Sci. 262:329–344

    Article  CAS  Google Scholar 

  18. 18.

    Vauthier C, Bouchemal K (2009) Methods for the preparation and manufacture of polymeric nanoparticles. Pharm. Res. 26:1025–1059

    Article  CAS  Google Scholar 

  19. 19.

    Zoromba MS, Abdel-Aziz MH, Bassyouni M, El-Ashtoukhy ESZ, Abdel-Hamid SMS (2019) Synthesis of o-aminophenol-m-phenylenediamine copolymer. J. Polym. Res. 26:34–42

    Article  CAS  Google Scholar 

  20. 20.

    Al-Hossainy AF, Zoromba MS (2019) Doped-poly (Para-nitroaniline- co aniline): synthesis, semiconductor characteristics, density, functional theory and photoelectric properties. J. Alloys Compd. 78:1–10

    Google Scholar 

  21. 21.

    Zoromba MS, Ismail MIM, Bassyouni M, Abdel-Aziz MH, Salah N, Alshahrie A, Memic A (2017) Fabrication and characterization of poly (aniline-co-o- anthranilic acid)/ magnetite nanocomposites and their application in wastewater treatment. Colloid Surface A: Physicochem Eng Aspects 520:121–130

    Article  CAS  Google Scholar 

  22. 22.

    Zoromba MS, Al-Hossainy AF, Abdel-Aziz MH (2017) Conductive thin films based on poly (aniline-co-o-anthranilic acid)/ magnetite nanocomposite for photovoltaic applications. Synth. Met. 231:34–43

    Article  CAS  Google Scholar 

  23. 23.

    Chen CH, KoC J, Chuang CH, Mao CF, Liao WT, Hsieh CD (2017) Synthesis and characterization of polyaniline co-doped with nitric acid and dodecyl benzene sulfonic acid. J. Polym. Res. 24:10–20

    Article  CAS  Google Scholar 

  24. 24.

    Al-Hossainy AF, Bassyouni M, Zoromba MSh (2018) Elucidation of Electrical and Optical Parameters of Poly(o-anthranilic acid)-poly(o-amino phenol)/Copper Oxide Nanocomposites Thin Films. J Inorg. Organomet. Polym. Mater 28: 2572–2583.

  25. 25.

    Abdel-Aziz MH, Al-Hossainy AF, Ibrahim A, Abd El-Maksoud SA, Zoromba MS, Bassyouni M, Abdel-Hamid SMS, Abd-Elmageed AAI, Elsayed IA, Alqahtani OM (2018) Synthesis, characterization and optical properties of multiwalled carbon nanotubes/aniline-o-anthranilic acid copolymer nanocomposite thin films. J. Mater. Sci. 29:16702–16714

    CAS  Google Scholar 

  26. 26.

    Thenmozhi G, Arockiasamy P, Santhi RJ (2014) Isomers of poly aminophenol: chemical synthesis, characterization, and its corrosion protection aspect on mild steel in 1M HCl. Int. J. Electrochem. Sci. 2014:1–12

    Article  CAS  Google Scholar 

  27. 27.

    Gu J, Kan S, Shen Q, Kan J (2014) Effects of Sulfanilic acid and Anthranilic acid on electrochemical stability of Polyaniline. Int. J. Electrochem. Sci. 9:6858–6869

    Google Scholar 

  28. 28.

    Li D, Kaner RB (2006) Shape and aggregation control of nanoparticles:not shaken, not stirred. J. Am. Chem. Soc. 128:968–975

    Article  CAS  Google Scholar 

  29. 29.

    Li G, Zhang C, Li Y, Peng H, Chen K (2010) Rapid polymerization initiated by redox initiator for the synthesis of polyaniline nanofibres. Polymer 51:1934–1939

    Article  CAS  Google Scholar 

  30. 30.

    Odian G (2004) Principles of polymerization4th edn. Wiley, Hoboken, p 216

    Google Scholar 

  31. 31.

    Tran HD, Wang Y, D’Arcy JM, Kaner RB (2008) Toward an understanding of the formation of conducting polymer nanofibers. ACS Nano 2:1841–1848

    Article  CAS  Google Scholar 

  32. 32.

    Ghonem MA, El-Enany G (2016) Development of coducing poly(o-amino phenol) film and its capacitance behaviour. Int. J. Electrochem. Sci. 11:9987–9997

    Article  CAS  Google Scholar 

  33. 33.

    Yakuphanoglu F, Basaran E, Senkal BF, Sezer E (2006) Electrical and optical properties of an organic semiconductor based on polyaniline prepared by emulsion polymerization and fabrication of Ag/polyaniline/n-SiSchottkydiode. J. Phys. Chem. B 110:16908–16913

    Article  CAS  Google Scholar 

  34. 34.

    Quillard S, Louarn G, Buisson JP, Boyer M, Lapkowski M, Pron A (1997) Vibrational spectroscopic studies of the isotope effects in polyaniline. Synth. Met. 84:805–806

    Article  CAS  Google Scholar 

  35. 35.

    Shaaban AF, Khalil AA, Radwan M, El-Hefnawy M, El-Khawaga HA (2017) Synthesis, characterization and application of a novel nanometer-sized chelating resin for removal of cu(II), co(II) and Ni(II) ions from aqueous solutions. J. Polym. Res. 62:24–165

    Google Scholar 

  36. 36.

    Saravanan C, Palaniappan S, Chandezon S (2008) Synthesis of nanoporous conducting polyaniline using ternary surfactant. J Mat Lett 62:882–885

    Article  CAS  Google Scholar 

  37. 37.

    Dufour B, Rannou P, Fedorko P, Djurado D, Travers JP, Pron A (2001) Effect of plasticizing dopants on spectroscopic properties, Supramolecular structure, and electrical transport in metallic Polyaniline. Chem. Mater. 13:4032–4040

    Article  CAS  Google Scholar 

  38. 38.

    Xia H, Wang Q (2002) Ultrasonic irradiation: a novel approach to prepare conductive polyaniline/nanocrystalline titanium oxide composites. Chem. Mater. 14:2158–2165

    Article  CAS  Google Scholar 

Download references

Author information



Corresponding author

Correspondence to A.M. Metwally.

Additional information

Publisher’s note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Metwally, A., Shaaban, A.F., Azab, M.M. et al. Synthesis, characterization, morphology and adsorption performance towards cu+2 ions of nano-sized copolymers of anthranilic acid and o-aminophenol poly(anthranilic acid-co-o-aminophenol). J Polym Res 27, 90 (2020).

Download citation


  • Polymeric nanoparticles (PNPs)
  • Copolymerizetion
  • Anthranilic acid
  • o-aminophenol
  • Ammonium peroxydisulfate (APS)
  • FeSO4.H2O
  • Adsorption